Rising gently from Massachusetts Avenue, Winthrop Road was laid out in 1894 as a real estate venture by F. Foster Sherburne, a member of the firm of Estabrook & Co., and a trustee of the Lexington Savings Bank. His family had been summer residents of Lexington for a number of years and at about this time other family members took up permanent residence in the Percy Road area.
In 1892 F.Foster Sherburne married Maud Tenney and the year before the wedding Sherburne built a large house at 1508 Massachusetts Avenue adjacent to her parents' house. In 1893 Maud's parents, Benjamin and Mary (Viles) Tenney, built themselves a new house as well (1536 Massachusetts Avenue, below), moving the old Meriam-Viles House that formerly stood on the property to 37-39 Woburn Street. Winthrop Road was laid out on the former Viles property, between the two houses.
Most of the dozen or so substantial houses along Winthrop Road were constructed between 1894 and 1907 for professional men who commuted into Boston and their families. One of the first buildings on the street was the house at 17 Winthrop Road (below), constructed in 1895 for Walter Rowse, a dye stuffs salesman.
|The house at 10 Winthrop (right) is one of Lexington's most unusual examples of the Shingle Style and displays an exaggerated and steeply-pitched gambrel roof, eyebrow window and shingled brackets.|
Both of Lexington's most prominent local late 19th century builders constructed homes in the neighborhood. David Tuttle built the houses at 1508 and 1536 Massachusetts Avenue and Abram C. Washburn was responsible for the construction of the houses at 9 & 16 Winthrop Road. At least three homes were designed by Lexington's highly original architect, Willard D. Brown. The houses at 11 and 15 Winthrop Road mix Colonial and Craftsman influences while the slightly later house at 20 Winthrop Road is a free interpretation of the Shingle Style with early 20th century Prairie and European influences.
Dating to 1904, the house at 21 Winthrop Road (below) is an unusual design combining elements of the Shingle Style with decorative gables popular in the English Revival.
The eclectic c. 1880 house at 1 Winthrop Road was moved to this site in the early 1920s from the west side of Pelham Road, just beyond the present Eliot Road.